N-bromobutanimide → HCID 178451611, 화합물

HRID 2383429노트

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HRID 2383429 반응식
[CH:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[NH:3][N:2]=1.[Br:21]N1C(=O)CCC1=O>ClCCl>[Br:21][C:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[NH:3][N:2]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 46836774tert-butyl 8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate

생성물 1

HCID 178451611HCID 178451611, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (0.301 g, 1.09 mmol) in dichloromethane (10 mL) was added N-bromosuccinimide (0.293 g, 1.64 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched by adding aqueous Na2CO3. The organic layer was separated, washed with brine (10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a residue. The crude product was purified by flash column chromatography (SiO2, 30% EtOAc in hexanes) to give the desired product. tert-butyl 1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (0.258 g, 67%) as a foamy white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.94 (s, 1H), 8.40 (s, 1H), 4.63 (s, 2H), 3.67 (m, 2H), 3.28 (m, 2H), 1.44 (s, 9H); LCMS [M+H]: 353.

후처리

  1. customThe reaction was quenched
  2. additionby adding aqueous Na2CO3
  3. customThe organic layer was separated
  4. washwashed with brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe crude product was purified by flash column chromatography (SiO2, 30% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-c2f7f5c3616e44f2ac96c44e7e1753b4
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263610B2

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